MONTREAL — It’s been five years since fans of the Boston Red Sox were able to cry for sympathy over their team’s failure to capture the ultimate goal. It’s arguable that BoSox backers never had more of a claim to the world of “woe is me” than supporters of the Chicago Cubs, but now there’s no doubt. Cubs fans are by far the most tortured souls in sports, as their team has gone more than 100 years without winning a World Series.

Boston Bruins defenseman Mark Stuart is among the masochists who root, root, root for the team from the North Side of Chicaog. He has been around for almost 25 of those 100 years — long enough to have felt the anguish that comes with wearing a red ‘C’ on your blue cap and also learn that nothing in sports is ever a foregone conclusion. That gives him great perspective heading into Game 4 of the Bruins’ Eastern Conference quarterfinal series with Montreal tomorrow night at Bell Centre. The Bruins are one win away from advancing to the second round of the Stanley Cup playoffs for the first time since 1999.

“You can’t think about that. You’ve got to win four, bottom line,” Stuart said today after the Bruins practiced. “We know they’re going to come out even harder tomorrow night and we’ve got play even better than we did last night. So we’re just looking at it as another game that we have to win.”

“Yeah, I think so. There are a lot of disappointments,” Stuart continued when asked to put his team’s current hockey team’s status with the history of his favorite diamond-dwelling club. “That’s true. Things are never done. You’ve got to win four. You never know what can happen.”

Luckily Stuart, a future NHL captain, is always affable — even when an annoying reporter wants to dredge up the Cubs’ nightmares of the past. As far as the worst collapses of his lifetime, Stuart said two are neck and neck for the title of biggest downer.

“There’s been a lot of them. Last year was really disappointing. They had such a good team,” explained Stuart, recalling last spring when a Cubs team with the second-best record in baseball lost in the first round of the MLB playoffs. “And then (Steve Bartman, who interfered with a would-be fly out in 2003). I feel bad for that kid, though. But that was disappointing. Thinking back on it, that didn’t lose it for them. But it’s just like, ‘ugh, what’s going to happen next?'”

A fellow Minnesota native, Bruins forward Blake Wheeler had the good sense to root for his hometown team rather than one with the world’s longest run of futility.

“The Twins, when they get there, they close the deal. I’ve been through playoff losses, not the heartbreak of a 3-0 deficit and lost (or similar dramatic defeat)” said Wheeler, who was 1 when the Twins won it all in ’87 but then was able to enjoy the club’s victory in the ’91 series.

That doesn’t mean that Wheeler and his non-Cubs-loving teammates lack the knowledge of what it’ll take to finish off the Habs.

“You never want to let your foot of the gas. I think that’s kind of the lesson you learn,” said Wheeler. “Anything’s possible this time of year. We want to take care of business like we do every game and just worry about every game and not worry about the fact that it’s 3-0 because we try to approach it every game at a time.”

If all goes according to plan, Stuart will raise the Stanley Cup later this postseason. But even with that accomplishment checked off his personal list of achievements, there will still be an open box next to the No. 1 thing he wants to witness as a sports fan.

“I’m just hoping in my lifetime,” said Stuart about a Cubs World Series title. “That’s all I care about.”